A river with a bridge, marina, and residential area.

Chesapeake City Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Chesapeake City holiday rentals

Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (25 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is HK$941
HK$2,302 total
includes taxes & fees
9 Aug - 10 Aug
Historic Chesapeake City Stay
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (43 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is HK$549
HK$873 total
includes taxes & fees
28 Jul - 29 Jul
Country Get Away Studio Apartment
Property grounds

Sunset River Cottage

Sunset River Cottage
Elkton
8.8 out of 10, Excellent, (18 reviews)
"The property was just what we needed. Very quiet, laid back and the pier was great for fishing!"
United States
Ray D.
The price is HK$2,152
HK$3,461 total
includes taxes & fees
25 Jul - 26 Jul
Sunset River Cottage
Interior

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
The price is HK$1,960
HK$2,323 total
includes taxes & fees
22 Jul - 23 Jul
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Terrace/patio

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (1 review)
"This unit is located behind a mansion /b&b. Had what we needed, clean, easy to access and Karin was helpful."
United States
Megan M.
The price is HK$1,482
HK$1,886 total
includes taxes & fees
22 Jul - 23 Jul
Tiny Home Tranquil Oasis
Terrace/patio

Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is HK$1,482
HK$1,839 total
includes taxes & fees
3 Aug - 4 Aug
Nature's Haven Tiny Home
Coffee/tea maker, fridge, microwave, oven

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
9.6 out of 10, Exceptional, (5 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is HK$1,058
HK$2,676 total
includes taxes & fees
27 Jul - 28 Jul
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Exterior

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
10.0 out of 10, Exceptional, (12 reviews)
"Clean and very home like. The backyard, well designed, it’s perfect to enjoy your morning coffee and a glass of wine at dinner. I will definitely come back and highly recommend this cozy place."
United States
Manjetjola P.
The price is HK$941
HK$1,263 total
includes taxes & fees
24 Jul - 25 Jul
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Dining

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark
9.6 out of 10, Exceptional, (23 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is HK$1,531
HK$2,611 total
includes taxes & fees
21 Jul - 22 Jul
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Exterior

Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (10 reviews)
"Place was very clean and the host was EXCELLENT with fast communication "
United States
Chris R.
The price is HK$2,371
HK$3,222 total
includes taxes & fees
28 Jul - 29 Jul
Elegant Family Stay • Quiet Neighborhood • Comfort
Terrace/patio

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.8 out of 10, Exceptional, (6 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is HK$1,279
HK$2,972 total
includes taxes & fees
17 Aug - 18 Aug
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Beach

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
The price is HK$1,205
HK$1,511 total
includes taxes & fees
27 Jul - 28 Jul
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is HK$533
HK$981 total
includes taxes & fees
21 Jul - 22 Jul
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Port Deposit
10.0 out of 10, Exceptional, (1 review)
"Renee & Pat were excellent hosts and we will definitely try to book again when in the area. Everything was as advertised and much more. Being pet friendly was a plus. We enjoyed two restaurants in the area while there, Lee's Landing and Old South Smokehouse, highly recommend!"
United States
Don S.
The price is HK$1,282
HK$1,456 total
includes taxes & fees
21 Jul - 22 Jul
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Smart TV

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (12 reviews)
"The house was very cozy and close to my venue Jennifer was very responsive with any questions nice place to stay roomy"
United States
Liza
The price is HK$1,524
HK$2,081 total
includes taxes & fees
22 Jul - 23 Jul
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Terrace/patio

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Charlestown
10.0 out of 10, Exceptional, (3 reviews)
"Had a wonderful stay. They really thought of everything. Had everything we could have possibly needed. It's a beautiful place and it was very clean and cared for."
United States
Laura K.
The price is HK$3,391
HK$5,105 total
includes taxes & fees
9 Aug - 10 Aug
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Exterior

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
9.8 out of 10, Exceptional, (49 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is HK$1,376
HK$1,658 total
includes taxes & fees
23 Jul - 24 Jul
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Smart TV

Cozy 1-bedroom apartment in Lincoln University

Cozy 1-bedroom apartment in Lincoln University
Lincoln University
The price is HK$924
HK$1,410 total
includes taxes & fees
10 Aug - 11 Aug
Cozy 1-bedroom apartment in Lincoln University
TV, books, stereo

Cozy House in a Quiet Neighborhood

Cozy House in a Quiet Neighborhood
Wilmington
The price is HK$1,164
HK$1,460 total
includes taxes & fees
10 Aug - 11 Aug
Cozy House in a Quiet Neighborhood
Interior

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (32 reviews)
"Perfect location for that town. "
United States
Hisham M.
The price is HK$1,294
HK$2,277 total
includes taxes & fees
21 Jul - 22 Jul
Private 3 room Queen Suite w/Kitchenette
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesapeake City Hotel Reviews

Embassy Suites by Hilton Newark Wilmington South

Embassy Suites by Hilton Newark Wilmington South

10/10 Excellent
"Q"
Ada 1-night trip
Posted less than an hour ago
Embassy Suites by Hilton Newark Wilmington South

Find out more about Chesapeake City

Search for holiday rentals in Chesapeake City on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake City using one of the methods below:

  • View our selection of featured holiday rentals in Chesapeake City
  • Use the map to find apartments and other holiday homes in the Chesapeake City neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesapeake City while they last

Look no further and take a look at our great range of rental properties in Chesapeake City!

Frequently asked questions

Can I find holiday rentals in Chesapeake City?

Yes, there are holiday rentals close to the most popular sights in Chesapeake City, or you can select a more secluded option if you're looking for a relaxing stay. Chesapeake City is known for its restaurants and waterfront. Make sure you have time to check out the museums while you're in the area.

What are some of the best holiday rentals that Chesapeake City has to offer?

HYDRANGEA HOUSE Waterview cozy 3-bdrm Getaway in quiet Chesapeake City AC & yard: This highly rated holiday home rental in Chesapeake City is located on a river, and has a patio, a selection of books and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Chesapeake City are Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun! and Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows .

How many holiday rentals are there in Chesapeake City?

With 10 Expedia holiday rentals, you're guaranteed to find just the right place for your Chesapeake City stay.

What can I see and do in Chesapeake City?

Cultural attractions include C and D Canal Museum, whereas Canal Wildlife Management Area is a spot to enjoy nature. While here, Chesapeake Inn Marina and Bohemia Bay Yacht Harbour are other places worth a visit.

What are holiday rentals like in Chesapeake City?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesapeake City. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip.